Lithium Hydroxide → HCID 66701982, compound

HRID 424697Notes

Reaction equation

HRID 424697 reaction equation
[OH-].[Li+].[CH2:3]([S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([C:21]2[O:25][C:24]([C:26]([O:28]C)=[O:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:14]=[C:13]([NH:30][C@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.O>[CH2:3]([S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([C:21]2[O:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=2)(=[O:19])=[O:20])[CH:14]=[C:13]([NH:30][C@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36])[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66702076HCID 66702076, compound

Product 1

HCID 66701982HCID 66701982, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (33 mg) was added to a solution of the subtitle product of step i) (0.23 g) in THF/H2O (1 ml/1 ml) and stirring maintained for 1 h. The THF was removed in vacuo and the residue neutralised with AcOH before extracting with EtOAc. The organics were then washed with H2O, dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase HPLC (gradient 95% to 20% 0.02M ammonium hydroxide/acetonitrile) to yield the title compound as an off-white solid. Yield: 0.14 g.

Workup

  1. temperaturemaintained for 1 h
  2. customThe THF was removed in vacuo
  3. extractionbefore extracting with EtOAc
  4. washThe organics were then washed with H2O
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC (gradient 95% to 20% 0.02M ammonium hydroxide/acetonitrile)

Sources & evidence

ORD record
ord-56766b565b6b44f5aa3ff983e2276fa7
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

Loading…